Background: Obese women are at high risk of early breastfeeding cessation, and health professionals (HPs) have a unique opportunity to provide them with breastfeeding support. Our objective was to describe HPs' experiences providing breastfeeding care for obese women during the prenatal, peripartum, and postpartum periods. Materials and Methods: In-depth, qualitative interviews were conducted with 34 HPs (including obstetricians, midwives, pediatricians, nurses, and lactation consultants) who care for pregnant or lactating women. They were recruited from a variety of settings in central New York. Interviews were audio-recorded, transcribed, verified for accuracy, and then analyzed qualitatively. Results: HPs identified obesity in multiple ways, some of which were consistent with standard cutoffs, whereas others implied extreme obesity. Nearly all HPs discussed ways they perceive obese women have challenges with breastfeeding. Some HPs described challenges as specific to obese women (e.g., limited mobility), whereas others described challenges as universal but more likely to occur among obese women (e.g., difficulties positioning the infant to breastfeed). Across professions, HPs described providing breastfeeding care for obese women as requiring more time and physical work and as being more challenging. HPs acknowledged stigma around obesity and discussed treating obese women with dignity and the same as other women. Strategies were suggested for improving breastfeeding support for obese women. Conclusions: HPs identified multiple challenges that obese women encounter with breastfeeding, as well as their own challenges with providing care. Comprehensive strategies are needed to assist obese women with breastfeeding and to alleviate strain on HPs who provide their care.